Dean and You (Male Reader Insert)
by Lopsided Whiskey Grin
Summary: Can you feel it? Can you feel the way he's touching you right there? He's taking his time, drawing it out. He's got you on your knees and face down in the mattress in the motel room you only got the keys to less than thirty minutes ago.


Can you feel it? Can you feel the way he's touching you right _there_? He's taking his time, drawing it out. He's got you on your knees and face down in the mattress in the motel room you only got the keys to less than thirty minutes ago. Your naked ass is up in the air and he's driving you out of your fucking mind, kneading his calloused fingers into the meat of your buttocks, pulling the cheeks apart and blowing soft puffs of air across your sensitive, exposed skin.

You try to think back to how you got here, but your brain is having a hard time focusing on that; it all happened so fast. One minute you were at the bar, flirting with a green-eyed stranger, hoping for some action, hoping you weren't reading him wrong. The next minute you were making out in his beautiful classic car, hot and heavy and with just the kind of urgency you were desperate for. And now you're in the motel room with him, naked and vulnerable and thrumming with anticipation, your dick aching and full where it hangs down between your legs, the leaking tip just barely brushing over the sheets.

He's kneeling on the bed behind you, naked just as you are, pressing up against you as his fingers continue to tease and massage. You can feel the hard, hot line of his cock pushing against the back of your thigh and it feels so fucking _good_. But it's not quite close enough to where you really want, is it? No, you want that dick buried so far in your ass you won't be able to walk right tomorrow. You want to feel the stretch and burn and oh god, his thumbs are at your rim now, pushing inside you just the slightest bit, the blunt edges of his fingernails scratching against your tight hole in the most amazing way.

Your breath catches and you moan out his name, the name you only just learned less than an hour ago, "Dean, fuckin' hell."

He chuckles a little hoarsely behind you and you feel his thumbs sink in a little deeper and begin to stretch you open. "You like that, Y/N? Yeah, you do," he chuckles again and then, "Reach up and grab me that lube. Wanna make sure you're nice and slick when I slide in there."

His words make you shudder, but you do as he asks. You reach up and grab a bottle of Astroglide tucked up by the pillows. Dean's cock just barely grazes the back of your low hanging, achingly full balls with the movement. You freeze instantly, on the very verge of coming apart without your dick having been touched even once yet.

Dean pulls his thumbs away, rubbing soothing circles on your hip, and after a moment and a few gulps of air you're able to get back into position and hand the bottle to Dean over your shoulder. He takes it wordlessly and the next instant you hear the cap cracking open and feel a cool stream of liquid being poured over your quivering asshole.

You yelp and fist your hands into the scratchy sheets beneath you and you work on controlling your breathing. Reaching beneath yourself, you squeeze at your weeping cock, feeling a small amount of relief with the pressure.

 _Please, please, please, oh god please just fuck me already_ you scream in your head. You need to be filled and you need it right fucking now.

You give voice to your anguish. "Please," you say, panting harshly and smearing precome up around the crown of your straining dick from where you're still gripping it. "Please, Dean."

Sweat breaks out on your brow and you screw your eyes shut as you feel his thumbs at your rim again. This time though he's not going slow, not teasing. He has a goal in mind as he artfully stretches you open and it's a goal you're both after: getting that cock buried inside you nice and deep.

Choking out a groan, you begin to stroke your dick. Dean's added fingers to replace his thumbs and soon you're taking three at a time. You hump your ass back, taking them as deep as you can and you can hear Dean suck in a sharp breath. He's as close to breaking as you are from the sounds of it.

The tinfoil tearing of a condom wrapper is the next sound you hear and you almost sob at the thought of your impending relief. Dean's fingers have not stopped pumping into you though and you know he must have used his teeth and free hand to rip open the rubber. This mental image alone is almost enough to have you busting your nut right then.

You pull in a deep breath to keep your orgasm at bay just a little longer. And then Dean's fingers are suddenly being pulled out of you and all the air in your lungs leaves you in a great rush. The blunt head of his cock is nudging against your lax hole now and you moan raggedly.

"Gotta get inside you," he rasps. His hands grip your cheeks and hold you open wide as he starts pushing in slowly. You shiver and your thighs start trembling when you hear him panting behind you.

But his cock is much bigger than the fingers he used to stretch you. The crown has just barely popped inside and the burn has turned into actual pain. "Wait, wait," you gasp into the sheets.

Dean stops immediately, his hands moving to your hips, trembling fingers tensing over your sweat-slick skin. It feels like he's trying to pull back out and you shake your head adamantly, glaring at him over your shoulder.

"Don't you fucking dare," you warn breathlessly. "Just give me a sec to get used to you, man. It's been awhile."

You can see the concern on his face, the way his brows are drawn together over those incredible green eyes and you know then what kind of man he really is. He's not some suave, smooth talking Dive-Bar Casanova, not really, not deep down. You can see and feel from the way he is holding back that he's caring, thoughtful, gentle, broken underneath that veneer. You know you'd love to see more of that side, if this was something that was going to last longer than just this one night. But you know it won't and you don't really mind. You didn't hit the bar tonight for anything other than hard and fast.

You look away from him and focus on relaxing and soon you feel your body become a little more lax. Dean's cock doesn't quite feel like it's going to split you open anymore and you readjust yourself on your knees.

"Okay," you say, giving him the go ahead to start pounding into you.

But he doesn't. His fingers flex on your hips and he pushes in slow, inch by inch. Your erection, which had been flagging a bit just a moment ago, comes back strong, filing to full capacity and making you lightheaded. It feels like he's been pushing inside you forever. Christ how long is that cock anyways?

Finally, _finally_ he bottoms out, pressing skin to skin. You let out a long, low moan almost at the exact same time Dean does. It feels incredible; you really have no other words to describe it. You have never felt so full in your life.

"F-fuck, Y/N," he breathes and you caution a look under yourself to where you're joined. It's a little crowded down there. Your heavy cock is swinging back and forth as Dean begins to pull out then thrust back in and his balls press against yours with each deep stroke. You can just make out his hairy thighs though, right behind your own.

Each pounding push forward rocks you on your knees and drives you ever closer to the edge. Dean's thick cock is brushing over your prostate with each plunge inside you and you stutter out his name raggedly as you continue pumping your dick. You're so close now, can't you feel it? There is a heavy pressure in your belly that keeps tightening with each thrust. It's moving down into your balls now, drawing them up to your body, ready to explode.

Dean has really started in on you now, desperately chasing after his release, pounding into you relentlessly. His hands move up to your shoulders, his fingers digging into the muscles there and you bow your back to take him even deeper.

It's the perfect angle and only two more rapid slams into your prostate and you're done for. "Dean," you cry, "Oh god, I'm gonna, I'm gonna-" You can't even finish the sentence before you're coming undone, shooting your load down onto the mattress in long pearly strings. Your body shakes with the force of it and you can barely hold yourself up anymore.

"I'm comin' too," Dean rasps, slamming in one more time and you almost swear you hear him say _Sammy_ but you're not really sure. He stiffens against you and you can feel his cock pulsing inside you, filling the condom and warming you in the most complete way and making you forget about him maybe calling you by the wrong name.

Your legs finally give out and you slump down onto the bed. Dean follows you down with a grunt, his softening dick still embedded in your ass. You both lay in a sweaty heap, breathing hard for a moment until Dean jerks up and away, his cock sliding wetly from you. Gasping, you repress a shiver at the suddenly empty feeling.

"Sorry," Dean says, "Didn't mean to crush you."

You brush your sweat-stiff hair from your forehead and look over at him. He's delicately pulling the used condom from his cock with a little cringe. You can understand the oversensitized feeling he must be experiencing because your whole body is an oversensitized mess at the moment too, your asshole especially. You know you won't be able to sit right for a few days and you couldn't be happier; it's exactly what you wanted when you went out tonight.

Watching Dean swagger into the bathroom, you hope he got what he wanted out of it too. You push off the bed when you hear the shower start and decide you'll help him wash up just to make sure.


End file.
